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Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates : Convenient Assembly of 6,7-Dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core. / Dar'in, Dmitry; Khoroshilova, Olesya; Kantin, Grigory; Krasavin, Mikhail.

в: Synthesis (Germany), Том 52, № 8, 17.04.2020, стр. 1266-1272.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Dar'in, D, Khoroshilova, O, Kantin, G & Krasavin, M 2020, 'Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Convenient Assembly of 6,7-Dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core', Synthesis (Germany), Том. 52, № 8, стр. 1266-1272. https://doi.org/10.1055/s-0039-1690802

APA

Dar'in, D., Khoroshilova, O., Kantin, G., & Krasavin, M. (2020). Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Convenient Assembly of 6,7-Dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core. Synthesis (Germany), 52(8), 1266-1272. https://doi.org/10.1055/s-0039-1690802

Vancouver

Dar'in D, Khoroshilova O, Kantin G, Krasavin M. Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Convenient Assembly of 6,7-Dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core. Synthesis (Germany). 2020 Апр. 17;52(8):1266-1272. https://doi.org/10.1055/s-0039-1690802

Author

Dar'in, Dmitry ; Khoroshilova, Olesya ; Kantin, Grigory ; Krasavin, Mikhail. / Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates : Convenient Assembly of 6,7-Dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core. в: Synthesis (Germany). 2020 ; Том 52, № 8. стр. 1266-1272.

BibTeX

@article{a3690d9dbfae49ac9c4c598afb17b3a6,
title = "Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates: Convenient Assembly of 6,7-Dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core",
abstract = "The first example of exploiting the trifunctional character of alkyl 4-chloro-2-diazo-3-oxobutanoates in the reactions with vicinal N, S-bis-nucleophiles leading to the formation of bicyclic 6,7-dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazines is presented. The key to the successful realization of the atom-economical synthetic strategy is the initial S N 2 event, which facilitates the subsequent domino 1,2,3-triazole formation via the Wolff reaction. Equally important is the choice of sodium acetate as the base: acetic acid formed in the course of the initial nucleophilic substitution acts as an efficient catalyst for the Wolff reaction, which suppresses the competing, unwanted fragmentation path (observed when other bases are used).",
keywords = "diazo transfer, domino reactions, multicenter reactions, nucleophilic substitution, Wolff 1,2,3-triazole synthesis",
author = "Dmitry Dar'in and Olesya Khoroshilova and Grigory Kantin and Mikhail Krasavin",
note = "Publisher Copyright: {\textcopyright} 2020 Georg Thieme Verlag. All rights reserved.",
year = "2020",
month = apr,
day = "17",
doi = "10.1055/s-0039-1690802",
language = "English",
volume = "52",
pages = "1266--1272",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "8",

}

RIS

TY - JOUR

T1 - Realizing the Trifunctional Potential of Alkyl 4-Chloro-2-diazo-3-oxobutanoates

T2 - Convenient Assembly of 6,7-Dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazine Core

AU - Dar'in, Dmitry

AU - Khoroshilova, Olesya

AU - Kantin, Grigory

AU - Krasavin, Mikhail

N1 - Publisher Copyright: © 2020 Georg Thieme Verlag. All rights reserved.

PY - 2020/4/17

Y1 - 2020/4/17

N2 - The first example of exploiting the trifunctional character of alkyl 4-chloro-2-diazo-3-oxobutanoates in the reactions with vicinal N, S-bis-nucleophiles leading to the formation of bicyclic 6,7-dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazines is presented. The key to the successful realization of the atom-economical synthetic strategy is the initial S N 2 event, which facilitates the subsequent domino 1,2,3-triazole formation via the Wolff reaction. Equally important is the choice of sodium acetate as the base: acetic acid formed in the course of the initial nucleophilic substitution acts as an efficient catalyst for the Wolff reaction, which suppresses the competing, unwanted fragmentation path (observed when other bases are used).

AB - The first example of exploiting the trifunctional character of alkyl 4-chloro-2-diazo-3-oxobutanoates in the reactions with vicinal N, S-bis-nucleophiles leading to the formation of bicyclic 6,7-dihydro-4 H-[1,2,3]triazolo[5,1-c][1,4]thiazines is presented. The key to the successful realization of the atom-economical synthetic strategy is the initial S N 2 event, which facilitates the subsequent domino 1,2,3-triazole formation via the Wolff reaction. Equally important is the choice of sodium acetate as the base: acetic acid formed in the course of the initial nucleophilic substitution acts as an efficient catalyst for the Wolff reaction, which suppresses the competing, unwanted fragmentation path (observed when other bases are used).

KW - diazo transfer

KW - domino reactions

KW - multicenter reactions

KW - nucleophilic substitution

KW - Wolff 1,2,3-triazole synthesis

UR - http://www.scopus.com/inward/record.url?scp=85082855691&partnerID=8YFLogxK

U2 - 10.1055/s-0039-1690802

DO - 10.1055/s-0039-1690802

M3 - Article

AN - SCOPUS:85082855691

VL - 52

SP - 1266

EP - 1272

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 8

ER -

ID: 52865623